Several compounds related in structure to the diol epoxides of naphthalene have recently been synthesized in our laboratory. These compounds are: 1beta-hydroxy-2alpha-methyl-3beta, 4beta-epoxy-1,2,3,4-tetrahydronaphthalene and its 3alpha, 4alpha-epoxy isomer, and 1beta-methyl-2alpha-hydroxy-3beta, 4beta-epoxy-1,2,3,4-tetrahydronaphthalene and its 3alpha,4alpha-epoxy isomer. We propose to carry out 1H NMR studies to determine the ground state conformations of these compounds. The solvolytic reactivities and solvolysis products from the above hydroxy methyl epoxides will also be determined, and compared with the results of the related diol epoxides in an effort to learn more about substituent and conformational effects in diol epoxide reactions. A collaborative study with Dr. D. M. Jerina of the National Institutes of Health on the solvolytic reactions of the diol epoxides and tetrahydroepoxides of benzo(a)pyrene and triphenylene will also be carried out.